For your first map, don't worry about colors. All the territories will be gray anyways- don't matter what you make them. As for the pencil, I recommend you used the pen(I believe it is so called) tool. It makes paths by points- you click, it marks a point. I'm explaining this really badly xD. As for the size, I'm not sure. Could you send a pic? I'll try to see what the issue is, and also circle the pen tool for you.
Note: Useful for when you get to making territories and bonuseshttps://www.warlight.net/Forum/10806-easy-tutorial-making-clean-map-borders
Edited 2/28/2016 21:49:17